Cystophloroketals A-E, Unusual Phloroglucinol-Meroterpenoid Hybrids from the Brown Alga Cystoseira tamariscifolia

被引：25

作者：

El Hattab, Mohamed ^{[1
]}

Genta-Jouve, Gregory ^{[2
,3
]}

Bouzidi, Naima ^{[1
]}

Ortalo-Magne, Annick ^{[4
]}

Hellio, Claire ^{[5
]}

Marechal, Jean-Philippe ^{[6
]}

Piovetti, Louis ^{[4
]}

Thomas, Olivier P. ^{[2
]}

Culioli, Gerald ^{[2
,4
]}

机构：

[1] Univ Blida 1, Lab Chim Subst Nat & Biomol, Blida, Algeria

[2] Univ Nice Sophia Antipolis, Fac Sci, CNRS, Inst Chim Nice,UMR 7272, Parc Valrose, F-06108 Nice 2, France

[3] Univ Paris 05, Fac Sci Pharmaceut & Biol, Sorbonne Paris Cite, Lab Pharmacognosie & Chim Subst Nat,CNRS,UMR 8638, F-75006 Paris, France

[4] Univ Toulon & Var, EA 4323, MAPIEM, F-83957 La Garde, France

[5] Univ Bretagne Occidentale, IUEM, UMR 6539, Biodimar LEMAR, F-29238 Brest, France

[6] Observ Milieu Marin Martiniquais, Schoelcher 97233, Martinique, France

来源：

JOURNAL OF NATURAL PRODUCTS | 2015年 / 78卷 / 07期

关键词：

DITERPENOID TOTAL-SYNTHESIS; ANTIFOULING ACTIVITY; MIXED BIOGENESIS; BIFURCARENONE; EXTRACTS; MERODITERPENOIDS; PHLOROTANNINS; BULLATENONE; METABOLITES; INHIBITOR;

D O I：

10.1021/acs.jnatprod.5b00264

中图分类号：

Q94 [植物学];

学科分类号：

071001 ;

摘要：

Cystophloroketals A-E (1-5), five new phloroglucinol-meroditerpenoid hybrids, have been isolated together with their putative biosynthetic precursor, the monocyclic meroditerpenoid 6, from the Mediterranean brown alga Cystoseira tamariscifolia. They represent the first examples of meroditerpenoids linked to a phloroglucinol through a 2,7-dioxabicyclo[3.2.1]octane moiety. The chemical structures, including absolute configurations, were elucidated on the basis of extensive spectroscopic analysis (HR-ESIMS, ID and 2D NMR, and ECD) and TDDFT ECD calculations. Compounds 1-6 were tested for their antifouling activity against several marine colonizing species (bacteria, fungi, invertebrates, micro- and macroalgae). Compound 6 showed high potency for the inhibition of macrofoulers (invertebrates and macroalgae), while cystophloroketals B (2) and D (4) displayed strong inhibition of the germination of the two macroalgae tested and moderate antimicrobial activities (bacteria, microalgae, and fungi).

引用

页码：1663 / 1670

页数：8

共 52 条

[21] CORNER FLAPPING - A SIMPLE AND FAST ALGORITHM FOR EXHAUSTIVE GENERATION OF RING CONFORMATIONS [J].